CN101842345A - 由甘油生产胺的方法 - Google Patents
由甘油生产胺的方法 Download PDFInfo
- Publication number
- CN101842345A CN101842345A CN200880113540A CN200880113540A CN101842345A CN 101842345 A CN101842345 A CN 101842345A CN 200880113540 A CN200880113540 A CN 200880113540A CN 200880113540 A CN200880113540 A CN 200880113540A CN 101842345 A CN101842345 A CN 101842345A
- Authority
- CN
- China
- Prior art keywords
- glycerine
- amino
- catalyzer
- piperazine
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims abstract description 490
- 235000011187 glycerol Nutrition 0.000 title claims abstract description 209
- 150000001412 amines Chemical class 0.000 title claims abstract description 61
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 90
- 239000001257 hydrogen Substances 0.000 claims abstract description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 59
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000003054 catalyst Substances 0.000 claims abstract description 49
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 45
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 45
- PZZICILSCNDOKK-UHFFFAOYSA-N propane-1,2,3-triamine Chemical compound NCC(N)CN PZZICILSCNDOKK-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229910052751 metal Inorganic materials 0.000 claims abstract description 21
- 239000002184 metal Substances 0.000 claims abstract description 21
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 150000003335 secondary amines Chemical class 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 230000000737 periodic effect Effects 0.000 claims abstract description 9
- 150000003141 primary amines Chemical class 0.000 claims abstract description 9
- 239000000654 additive Substances 0.000 claims abstract description 4
- 230000000996 additive effect Effects 0.000 claims abstract description 4
- 239000004568 cement Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 168
- 238000000034 method Methods 0.000 claims description 91
- 239000000203 mixture Substances 0.000 claims description 71
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 64
- 238000002360 preparation method Methods 0.000 claims description 33
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 30
- GHAIYFTVRRTBNG-UHFFFAOYSA-N piperazin-1-ylmethanamine Chemical compound NCN1CCNCC1 GHAIYFTVRRTBNG-UHFFFAOYSA-N 0.000 claims description 29
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 claims description 24
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 23
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 22
- 230000015572 biosynthetic process Effects 0.000 claims description 17
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 claims description 17
- 150000004885 piperazines Chemical class 0.000 claims description 16
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 15
- PLGYKYHVPUUNAM-UHFFFAOYSA-N 1,6-dimethylpiperazin-2-amine Chemical compound NC1N(C(CNC1)C)C PLGYKYHVPUUNAM-UHFFFAOYSA-N 0.000 claims description 14
- 238000004821 distillation Methods 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 13
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 12
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 12
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 11
- 150000004985 diamines Chemical class 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- QEKPBYCXURULNE-UHFFFAOYSA-N 2-aminopropane-1,1-diol Chemical compound CC(N)C(O)O QEKPBYCXURULNE-UHFFFAOYSA-N 0.000 claims description 8
- CGFARGCLHNISDM-UHFFFAOYSA-N 1,5-dimethylpiperazin-2-amine Chemical compound NC1N(CC(NC1)C)C CGFARGCLHNISDM-UHFFFAOYSA-N 0.000 claims description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 7
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 claims description 6
- 239000001294 propane Substances 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 238000012272 crop production Methods 0.000 claims description 4
- 239000004744 fabric Substances 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000004902 Softening Agent Substances 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 239000004848 polyfunctional curative Substances 0.000 claims description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 2
- 239000000057 synthetic resin Substances 0.000 claims description 2
- 229920003002 synthetic resin Polymers 0.000 claims description 2
- 238000004073 vulcanization Methods 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- 150000002739 metals Chemical class 0.000 abstract 2
- YWDBOOQOEFVBRX-UHFFFAOYSA-N (6-methylpiperazin-2-yl)methanamine Chemical compound CC1CNCC(CN)N1 YWDBOOQOEFVBRX-UHFFFAOYSA-N 0.000 abstract 1
- JOYZWWYHLNKUEF-UHFFFAOYSA-N [5-(aminomethyl)piperazin-2-yl]methanamine Chemical compound NCC1CNC(CN)CN1 JOYZWWYHLNKUEF-UHFFFAOYSA-N 0.000 abstract 1
- OZVFCGNUWQMKGY-UHFFFAOYSA-N [6-(aminomethyl)piperazin-2-yl]methanamine Chemical compound NCC1CNCC(CN)N1 OZVFCGNUWQMKGY-UHFFFAOYSA-N 0.000 abstract 1
- 239000012018 catalyst precursor Substances 0.000 description 53
- 239000000463 material Substances 0.000 description 31
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000007789 gas Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000007787 solid Substances 0.000 description 24
- 230000003197 catalytic effect Effects 0.000 description 22
- 238000004587 chromatography analysis Methods 0.000 description 18
- 239000010949 copper Substances 0.000 description 18
- 238000005576 amination reaction Methods 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- -1 glyceryl amine Chemical class 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
- 229910052802 copper Inorganic materials 0.000 description 14
- 229910052759 nickel Inorganic materials 0.000 description 14
- 238000001556 precipitation Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000011572 manganese Substances 0.000 description 11
- 229910017052 cobalt Inorganic materials 0.000 description 10
- 239000010941 cobalt Substances 0.000 description 10
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 10
- 238000007598 dipping method Methods 0.000 description 10
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000001354 calcination Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 229910052748 manganese Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 229910052707 ruthenium Inorganic materials 0.000 description 7
- 229910052726 zirconium Inorganic materials 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229910002804 graphite Inorganic materials 0.000 description 6
- 239000010439 graphite Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 229910052728 basic metal Inorganic materials 0.000 description 5
- 150000003818 basic metals Chemical class 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 229910052741 iridium Inorganic materials 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910044991 metal oxide Inorganic materials 0.000 description 5
- 150000004706 metal oxides Chemical class 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 235000011118 potassium hydroxide Nutrition 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
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- 239000000725 suspension Substances 0.000 description 5
- 230000004304 visual acuity Effects 0.000 description 5
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229910012851 LiCoO 2 Inorganic materials 0.000 description 4
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 4
- 229910002651 NO3 Inorganic materials 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 239000003225 biodiesel Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 3
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- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 3
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- 238000012856 packing Methods 0.000 description 2
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- 239000011574 phosphorus Substances 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- PBCFLUZVCVVTBY-UHFFFAOYSA-N tantalum pentoxide Inorganic materials O=[Ta](=O)O[Ta](=O)=O PBCFLUZVCVVTBY-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- 238000007669 thermal treatment Methods 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 1
- LSRUBRSFDNKORM-UHFFFAOYSA-N 1,1-diaminopropan-1-ol Chemical compound CCC(N)(N)O LSRUBRSFDNKORM-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
- RIUXWEGBWYUUEF-UHFFFAOYSA-N 4-bromo-2-cyclopropyl-1h-pyrrolo[2,3-b]pyridine Chemical compound C=1C=2C(Br)=CC=NC=2NC=1C1CC1 RIUXWEGBWYUUEF-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZKBSDMGDEJPNGS-HSHFZTNMSA-N C(C(O)CO)(=O)O.C([C@H](O)CO)(=O)O Chemical compound C(C(O)CO)(=O)O.C([C@H](O)CO)(=O)O ZKBSDMGDEJPNGS-HSHFZTNMSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- LWQRRZURZCYGAJ-UHFFFAOYSA-N NC1CN(C(CN1)C)C Chemical compound NC1CN(C(CN1)C)C LWQRRZURZCYGAJ-UHFFFAOYSA-N 0.000 description 1
- GRXMKSIKWKCLSE-UHFFFAOYSA-N NC1CN(CC(N1)C)C Chemical compound NC1CN(CC(N1)C)C GRXMKSIKWKCLSE-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000003483 aging Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- 239000000109 continuous material Substances 0.000 description 1
- WXYNCCWBUXKSBG-UHFFFAOYSA-N copper;nitric acid Chemical compound [Cu].O[N+]([O-])=O WXYNCCWBUXKSBG-UHFFFAOYSA-N 0.000 description 1
- 238000009295 crossflow filtration Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical group CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910021518 metal oxyhydroxide Inorganic materials 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- XNHGKSMNCCTMFO-UHFFFAOYSA-D niobium(5+);oxalate Chemical compound [Nb+5].[Nb+5].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O XNHGKSMNCCTMFO-UHFFFAOYSA-D 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- DYIZHKNUQPHNJY-UHFFFAOYSA-N oxorhenium Chemical compound [Re]=O DYIZHKNUQPHNJY-UHFFFAOYSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 238000000247 postprecipitation Methods 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- BLTPNRTWCHWASU-UHFFFAOYSA-N propane-1,1,1-triamine Chemical compound CCC(N)(N)N BLTPNRTWCHWASU-UHFFFAOYSA-N 0.000 description 1
- ZNZJJSYHZBXQSM-UHFFFAOYSA-N propane-2,2-diamine Chemical class CC(C)(N)N ZNZJJSYHZBXQSM-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910003449 rhenium oxide Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/023—Preparation; Separation; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07115214 | 2007-08-29 | ||
| EP07115214.4 | 2007-08-29 | ||
| PCT/EP2008/060741 WO2009027248A1 (de) | 2007-08-29 | 2008-08-15 | Verfahren zur herstellung von aminen aus glycerin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101842345A true CN101842345A (zh) | 2010-09-22 |
Family
ID=39802803
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200880113540A Pending CN101842345A (zh) | 2007-08-29 | 2008-08-15 | 由甘油生产胺的方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20100240894A1 (ja) |
| EP (1) | EP2185499A1 (ja) |
| JP (1) | JP2010536913A (ja) |
| CN (1) | CN101842345A (ja) |
| BR (1) | BRPI0815779A2 (ja) |
| RU (1) | RU2480449C2 (ja) |
| WO (1) | WO2009027248A1 (ja) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103739501A (zh) * | 2014-01-14 | 2014-04-23 | 南京嵘天绿色化学有限公司 | 一种甘油仲羟基氨基化的方法 |
| WO2018032522A1 (zh) * | 2016-08-18 | 2018-02-22 | 万华化学集团股份有限公司 | 用于聚醚胺合成的负载型催化剂及其制备方法 |
| CN112638890A (zh) * | 2018-08-30 | 2021-04-09 | 罗地亚经营管理公司 | 直接胺化制备丙酮缩甘油胺的方法 |
| CN114315605A (zh) * | 2020-10-09 | 2022-04-12 | 中石化南京化工研究院有限公司 | 水基钻井液用胺类插层抑制剂及其制备方法 |
| CN116655478A (zh) * | 2023-07-27 | 2023-08-29 | 内蒙古圣氏化学股份有限公司 | 一种连续化生产1,3-二氨基-2-丙醇的方法 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010052181A2 (de) * | 2008-11-05 | 2010-05-14 | Basf Se | Verfahren zur herstellung von n,n-substituierten-3-aminopropan-1-olen |
| EP2379488B1 (de) | 2008-12-19 | 2013-02-20 | Basf Se | Verfahren zur herstellung von reinem triethanolamin (teoa) |
| JP5689078B2 (ja) | 2009-03-12 | 2015-03-25 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | １−アダマンチルトリメチルアンモニウム水酸化物の製造方法 |
| WO2011049660A1 (en) * | 2009-10-19 | 2011-04-28 | Dow Global Technologies Inc. | Process for preparing a 1,2-ethylenediamine or 1,2-propylenediamine |
| US9999690B2 (en) | 2013-11-08 | 2018-06-19 | Perosphere Pharmaceuticals Inc. | Labeled compounds and methods of imaging, diagnosing cartilage disorders and diseases, and monitoring cartilage health using labeled and unlabeled compounds |
| CN104693038B (zh) * | 2013-12-06 | 2017-07-28 | 中国科学院大连化学物理研究所 | 一种以丙二醇和液氨为原料制备丙二胺的方法及其装置 |
| JP6200314B2 (ja) * | 2013-12-25 | 2017-09-20 | 花王株式会社 | 水硬性組成物用添加剤組成物 |
| JP6200315B2 (ja) * | 2013-12-25 | 2017-09-20 | 花王株式会社 | 水硬性組成物用添加剤組成物 |
| EP2995607A1 (en) | 2014-09-10 | 2016-03-16 | Taminco bvba | Direct amination of alcohols with heteropoly acids |
| WO2019020488A1 (en) * | 2017-07-26 | 2019-01-31 | Basf Se | PROCESS FOR THE PREPARATION OF 3-AMINO-1,2-PROPANDIOL AND ITS DERIVATIVES |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB844448A (en) * | 1956-03-23 | 1960-08-10 | Sugar Res Foundation Inc | Reductive aminolysis process |
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| US3723529A (en) * | 1970-10-19 | 1973-03-27 | Jefferson Chem Co Inc | Decolorization of polyethylene polyamines |
| US4234730A (en) * | 1979-09-24 | 1980-11-18 | Texaco Development Corp. | Process of preparing selective mixtures of piperazine and ethylenediamine |
| SU893940A1 (ru) * | 1980-03-31 | 1981-12-30 | Проектный и научно-исследовательский институт "Ростовский ПромстройНИИпроект" | Комплексна добавка |
| GB8819663D0 (en) * | 1988-08-18 | 1988-09-21 | Bp Chem Int Ltd | Chemical process |
| DE4325847A1 (de) * | 1993-07-31 | 1995-02-02 | Basf Ag | Kobaltkatalysatoren |
| CA2134009C (en) * | 1993-11-11 | 2005-03-08 | Oleg Werbitzky | Bicyclic amidines, process for their preparation, and their use as catalyst |
| DE4428004A1 (de) * | 1994-08-08 | 1996-02-15 | Basf Ag | Verfahren zur Herstellung von Aminen |
| ES2169169T3 (es) * | 1995-05-09 | 2002-07-01 | Basf Ag | Catalizadores de cobalto. |
| MX9708720A (es) * | 1995-05-17 | 1997-12-31 | Basf Ag | Preparacion de n-metil-2-(3,4-dimetoxifenil) etilamina. |
| SE513250C2 (sv) * | 1997-11-11 | 2000-08-07 | Akzo Nobel Nv | Amineringsförfarande för framställning av polyaminer |
| GB2332202A (en) * | 1997-12-09 | 1999-06-16 | Courtaulds Coatings | Curable epoxy resin compositions |
| RU2149851C1 (ru) * | 1998-09-09 | 2000-05-27 | Концерн "Еврософт" | Бетонная смесь |
| DE50007278D1 (de) * | 1999-12-06 | 2004-09-09 | Basf Ag | Verfahren zur Herstellung von Aminen |
| DE10153410A1 (de) * | 2001-10-30 | 2003-05-15 | Basf Ag | Verfahren zur Auftrennung von wasserhaltigen Rohamingemischen aus der Aminsynthese |
| DE10160143A1 (de) * | 2001-12-07 | 2003-06-18 | Basf Ag | Verfahren zur selektiven Hydrierung von olefinisch ungesättigten Carbonylverbindungen |
| WO2007104663A1 (de) * | 2006-03-10 | 2007-09-20 | Basf Se | Mischoxid-katalysatoren |
-
2008
- 2008-08-15 US US12/675,413 patent/US20100240894A1/en not_active Abandoned
- 2008-08-15 EP EP08787269A patent/EP2185499A1/de not_active Withdrawn
- 2008-08-15 JP JP2010522307A patent/JP2010536913A/ja active Pending
- 2008-08-15 CN CN200880113540A patent/CN101842345A/zh active Pending
- 2008-08-15 BR BRPI0815779-0A2A patent/BRPI0815779A2/pt not_active IP Right Cessation
- 2008-08-15 WO PCT/EP2008/060741 patent/WO2009027248A1/de active Application Filing
- 2008-08-15 RU RU2010111554/04A patent/RU2480449C2/ru not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB844448A (en) * | 1956-03-23 | 1960-08-10 | Sugar Res Foundation Inc | Reductive aminolysis process |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103739501A (zh) * | 2014-01-14 | 2014-04-23 | 南京嵘天绿色化学有限公司 | 一种甘油仲羟基氨基化的方法 |
| CN103739501B (zh) * | 2014-01-14 | 2016-01-20 | 南京嵘天绿色化学有限公司 | 一种甘油仲羟基氨基化的方法 |
| WO2018032522A1 (zh) * | 2016-08-18 | 2018-02-22 | 万华化学集团股份有限公司 | 用于聚醚胺合成的负载型催化剂及其制备方法 |
| US11045794B2 (en) | 2016-08-18 | 2021-06-29 | Wanhua Chemical Group Co., Ltd. | Supported catalyst used for synthesizing polyether amine, and manufacturing method |
| CN112638890A (zh) * | 2018-08-30 | 2021-04-09 | 罗地亚经营管理公司 | 直接胺化制备丙酮缩甘油胺的方法 |
| CN114315605A (zh) * | 2020-10-09 | 2022-04-12 | 中石化南京化工研究院有限公司 | 水基钻井液用胺类插层抑制剂及其制备方法 |
| CN114315605B (zh) * | 2020-10-09 | 2024-04-02 | 中石化南京化工研究院有限公司 | 水基钻井液用胺类插层抑制剂及其制备方法 |
| CN116655478A (zh) * | 2023-07-27 | 2023-08-29 | 内蒙古圣氏化学股份有限公司 | 一种连续化生产1,3-二氨基-2-丙醇的方法 |
| CN116655478B (zh) * | 2023-07-27 | 2023-10-10 | 内蒙古圣氏化学股份有限公司 | 一种连续化生产1,3-二氨基-2-丙醇的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0815779A2 (pt) | 2015-02-24 |
| EP2185499A1 (de) | 2010-05-19 |
| WO2009027248A1 (de) | 2009-03-05 |
| JP2010536913A (ja) | 2010-12-02 |
| RU2010111554A (ru) | 2011-10-10 |
| US20100240894A1 (en) | 2010-09-23 |
| RU2480449C2 (ru) | 2013-04-27 |
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